


It Never Woulda Worked Out Anyway

by the_only_education_worth_having



Category: Supernatural
Genre: Bars, Brad Paisley - Freeform, Cuddles, Drinking, F/M, Feelings, Fluff, Friendship, Rejection, Sabotage, Song fic, admitting to feelings, new relationships, playing pool
Language: English
Status: Completed
Published: 2020-02-13
Updated: 2020-02-13
Packaged: 2021-02-28 07:01:51
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,204
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22699834
Author URL: https://archiveofourown.org/users/the_only_education_worth_having/pseuds/the_only_education_worth_having
Summary: Dean spills a secret
Relationships: Dean Winchester/Reader, Dean Winchester/You
Kudos: 23





	1. Chapter 1

Y/N stood in the bathroom of the bar looking at herself in the small scratched mirror on the wall. She got a small tub out of her bag and popped a couple mints in her mouth before leaning in towards the mirror to top up her lipstick, quickly checking none of it was on her teeth. She sprayed perfume on her fingers and dabbed it on her wrist and behind her ears hoping it covered any smells that clung to her from this dive bar. After a quick comb of her hair with her fingers and a rearrangement of her cleavage, she headed back into the bar. She walked towards the stool she had been sitting on to find the guy she had been talking to, Jake, stood up downing his beer and placing some banknotes on the bar.

‘Hey,’ Y/N said tucking her purse under her arm as she smiled and said, ‘you ready to get out of here?’ Jake looked at her uneasily and paused for a second before he shook his head and said, ‘actually I think I’m gonna head home.’  
‘Oh,’ Y/N said her face dropping for a moment before she plastered on a fake smile and said, ‘cool.’  
‘Look you’re a nice girl it’s just I’ve got to get up early and-‘  
‘No need to explain,’ she waved though she couldn’t help but feel shot down. They had been chatting for nearly an hour and after a bad hunt, all she wanted was to relax and have some fun. They had seemed to be clicking and it felt as if it was going somewhere good before she went to the bathroom.  
‘You better get going it’s late,’ she said turning to the bar and climbing up on her stool.  
‘Y/N I really am sorry,’ he said touching her shoulder gently, ‘really.’  
‘Whatever,’ she said not looking at him as she raised her arm for the bartender, ‘no biggie.’

She waited for a moment before she finally allowed herself to check to see if he was gone. There was no one next to her. As the bartender approached she went to order but a voice came from behind her and interrupted, ‘two beers please.’  
She turned and found Dean sitting down beside her with a smile. She smiled back.  
‘Hey,’ he said, ‘where’s your friend?’  
‘Gone,’ she replied flatly.  
‘Thought you weren’t coming back to the motel tonight.’  
‘Well that was the plan,’ she sighed, ‘he must have got a better offer.’  
‘Pffft, I don’t think there’s a better offer,’ he said nudging her shoulder with his and throwing her a wink.  
‘Yeah, yeah,’ she said swigging from the bottle that had been placed in front of her a moment ago.  
‘C’mon don’t be all mopey. So one guy blew you off, big deal,’ Dean said, ‘let’s get drunk and play some pool and by the end of the night you won’t even remember that guy’s name.’

Dean stood up and grabbed his beer in one hand and reached out and took her hand in his tugging her off her seat. She allowed herself to be walked through the bar as she chugged her beer. He led her to the pool table which was thankfully deserted and they parted ways. Dean shed his leather jacket and placed it on a stool towards the wall as he picked up a cue from the rack. Y/N followed suit and copied his movements coming to stand by the table with a smaller cue and beer bottle in hand.

‘So usual rules. Best of five. Loser pays the bar tab and gets us some food on the way home,’ Dean said as he lined up the rack on the table.  
‘Who’s breaking?’ He asked, ‘I’m happy for ladies first.’  
‘I’ll let you,’ she said, ‘seeing as I’m gonna whoop your ass.’  
‘Please,’ Dean scoffed moving to the other end of the table where he took a moment to line up his cue and made the first strike. The balls parted with a loud crack and scattered across the table though to his dismay none of them landed in a pocket, ‘damn it.’

Y/N chuckled and walked to where Dean was standing to nudge him out of the way with her hip as she bent over and lined up a shot sinking a striped ball into the corner pocket, ‘told ya.’

They played for ages each round getting more and more heated as the competition stayed neck and neck. By the last round, Y/N had completely forgotten about the guy from before thanks to Dean. Well, Dean and the alcohol.

They both had two balls left to pot in their last round and Dean was first up. He moved to look for the best angle to hit from. He stationed himself almost across the entire table lining up the perfect shot. He looked up at Y/N who was watching him. She looked defeated knowing that Dean was going to sink both balls and win. Dean faltered. He went to hit the ball and it shot forward hitting the corner of the pocket and bouncing off. He fumbled the shot.

Y/N cheered and rushed forward to take her shot. Quick as a flash she had sunk her own ball and the black finishing the game. She jumped back from the table and cheered throwing her arms above her head and closing her eyes. Dean watched her with a wry smile as she walked towards him and said, ‘pay the barman chump. I’m gonna go pee before you take me for food.’

And she turned flipping her hair in his face and strutted away. Dean watched her with a smile. Though he’d lost he didn’t really care. She was happy and that was all that mattered.


	2. Chapter 2

When Y/N appeared from the bathroom she couldn’t find Dean anywhere in the crowd of people and so headed outside where she found him resting against the wall watching the world go by. She sidled up beside him and rested on the wall watching him as he glimpsed at her for a moment. The bar came out to a parking lot which connected to the main road where cars still whizzed past even though it was into the early hours. 

‘You ready to go?’ Dean asked standing up tall which made him loom above her.   
‘Yeah,’ she said following him as he started walking towards the sidewalk on the other side of the car park. They walked in comfortable silence to the pizza shop and then to the motel with only a small amount of chit chat. Though this wasn’t awkward it did allow Y/N to go into her thoughts and think about being blown off earlier. The motel was in darkness as they got back and as Dean went around switching the wall lights on Y/N panned out on her bed watching him. Dean sat on her bed resting on the headboard as he placed the pizza box on the bed and switched on the tv. Y/N pushed both shoes off, which landed with a clunk on the floor and rolled onto her front grabbing a slice of pizza and chomping the end off. 

‘You okay?’ Dean mumbled with a mouth full of food.   
‘Mmhmm,’ Y/N replied.  
‘Only you’ve been pretty quiet since we left the bar,’ Dean said, ‘I thought I was the one who was supposed to be pouting. I mean you’ve got quite a talent at running up a bar tab I thought you’d be happy at escaping footing the bill.’  
‘I’m happy,’ she said though her face dropped, ‘I mean I knew it was a sure thing so it kinda takes the fun out of it.’  
‘Please, I was just having an off night,’ Dean scoffed.  
‘Me too,’ she sighed.

She climbed up on her knees and scooted to the headboard sitting next to Dean and watching the tv which was playing an old cheers rerun. Dean said nothing for a moment and then turned towards her and said, ‘wait, is this about the guy from the bar? I thought you didn’t care about that.’  
‘I didn’t… it’s just it’s not just that one guy. It seems every guy I’m interested in lately has no interest in me. Like I’ve lost my mojo.’  
‘Oh stop it. You’ve not lost anything. I mean it’s probably for the best they were put off it’s not like it would have worked out anyway.’  
‘Yeah you’re right,’ she sighed, ‘it’s not as though I’m looking to get married or anything though wait what do you mean put off?’  
Dean fell silent before he shrugged and said, ‘I don’t know there just must’ve been something that changed their mind.’  
He swigged his beer and turned his eyes to the TV but Y/N refused to let it go and turned it off. 

‘What did you do?’ She said cocking an eyebrow as Dean turned to look at her.  
‘What do you mean?’  
‘I mean you’ve been awful nice all evening. Regular Dean would’ve told me to walk it off. Why would you think there was something that out the guys off?   
‘Well…I just mean that…okay,’ Dean sighed, ‘I didn’t mean for it to happen as much as it did.’  
‘What did you do?’  
‘Okay, so I might have told the guy you were talking to that you were probably excited to go home with him because you’ve just got out of the joint.’  
‘What?!’ Y/N shrieked, ‘why would you do that?’  
‘I was just looking out for you that guy looked sleazy.’  
‘Evidently not that sleazy seeing as he didn’t want to date a jailbird! How could you! It’s got nothing to do with you who I sleep with.’  
‘I’m sure they didn’t really believe what I said’  
‘Well, he sure left quick enough-. Wait what do you mean ‘they’? Oh my god, this is not the first time is it?’

Dean’s eyes dropped down as he reached for another piece of pizza which Y/N snatched out of his hand and threw back in the box.   
‘Dean!’  
‘Okay, I might have done this a few times.’  
‘Like when?’  
‘The guy in Sacramento.’  
‘What did you say?’  
‘You’d have to get back to your kids soon. All seven.’  
‘Jesus! The guy in Fort Lauderdale too?’  
‘Told him you were a stripper.’  
‘Jacksonville?’  
‘That you spend most of your time in seedy motels. Which is technically not a lie!’ Dean reasoned as Y/N got up off the bed and started pacing. Dean remained on the bed wincing he knew that face, she was seething.

‘How could you think this was okay Dean!’ She shouted.  
‘I don’t know,’ Dean muttered.  
‘What possible reason could you have to meddle in my love life! I don’t interfere with every bimbo you parade through here!’  
‘Because I care about you!’  
‘You don’t think I care about you? About Sam? Of course, I do but that’s not caring Dean, that’s psychotic!’  
‘What do you want me to say Y/N?’  
‘The truth!’ Y/N said.  
‘Because I’m jealous okay!’  
The air hung heavy for a moment as the two of them looked at each other in disbelief. Y/N’s face fell into shock as did Dean’s as he realised what he’d said.  
‘Y/N listen I didn’t mean,’ Dean stuttered.  
‘Jealous…’ she whispered, ‘why are you jealous? I mean do you like me? Do you just not want guys around?’  
‘I don’t know,’ Dean said as Y/N sat down on the edge of the bed looking at him.  
‘Dean..’  
‘I just thought I was doing you a favour at first and then I thought it was because we’re a team and then I realised that I sorta wanted to be the guy you were flirting with.’

She sighed and looked at him. She didn’t know what to say. She knew he was stunningly attractive. He was funny, smart and caring but she had never actually thought of him in that way. They’d been friends forever.

‘Look, Dean,’ she said.  
‘Look you don’t have to let me down easy okay.’  
‘I’m not letting you down easy,’ she insisted, ‘I just never thought about us that way.’  
‘It’s fine. Really.’  
‘Would you let me talk? Look I’m not gonna day yeah I wanna jump head into a relationship with you there’s loads of stuff to consider I mean we work together for one and it’s not as if we can get away from each other if it ends badly.’  
‘I get that,’ Dean said, ‘that’s why I never said anything before now.’  
Y/N climbed on the bed and cuddled into his side.   
‘I’m not saying no,’ she whispered, ‘I’m just saying let me think about it first…’  
‘Okay,’ Dean said kissing the top of her head.  
‘Besides you might be my only option given that I’m a stripper who’s just got out of prison and is looking after seven kids.’  
‘True,’ Dean chuckled as he wrapped an arm around her and pulled her towards him, even if she was shooting him down this was better than being yelled at.


End file.
